Iodoethane → HCID 58841173, compound

HRID 1269355Notes

Reaction equation

HRID 1269355 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]([O:11][CH2:12]/[C:13](/[C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1)=[C:14](/[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)\[C:15]([OH:17])=[O:16])=[O:10].[CH2:34](I)[CH3:35].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]([O:11][CH2:12]/[C:13](/[C:24]1[CH:25]=[CH:26][C:27]([S:30]([CH3:33])(=[O:31])=[O:32])=[CH:28][CH:29]=1)=[C:14](/[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)\[C:15]([O:17][CH2:34][CH3:35])=[O:16])=[O:10]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 18448169HCID 18448169, compound

Product 1

HCID 58841173HCID 58841173, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.6 g of (2Z)-4-({[(6-bromohexyl)oxy]carbonyl}oxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoic acid in 20 mL of DMF at rt was added 3.8 mL of ethyl iodide and 670 mg of potassium carbonate under nitrogen. The reaction was stirred for 1 h, quenched by saturated aqueous NH4Cl, extracted with EtOAc, washed with water (3×), brine, and dried over sodium sulfate. Purification by flash chromatography afforded 1.86 g of the titled compound as a brownish oil.

Workup

  1. customquenched by saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washwashed with water (3×), brine
  4. dry with materialdried over sodium sulfate
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-68f84cf9eb24406eb5996716a2edc563
Source dataset
uspto-grants-2007_04
Patent number
US07199154B2

Reaction notes

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